7-deoxyloganetic acid synthase catalyzes a key 3 step oxidation to form 7-deoxyloganetic acid in Catharanthus roseus iridoid biosynthesis

Phytochemistry. 2014 May:101:23-31. doi: 10.1016/j.phytochem.2014.02.009. Epub 2014 Mar 1.

Abstract

Iridoids are key intermediates required for the biosynthesis of monoterpenoid indole alkaloids (MIAs), as well as quinoline alkaloids. Although most iridoid biosynthetic genes have been identified, one remaining three step oxidation required to form the carboxyl group of 7-deoxyloganetic acid has yet to be characterized. Here, it is reported that virus-induced gene silencing of 7-deoxyloganetic acid synthase (7DLS, CYP76A26) in Catharanthus roseus greatly decreased levels of secologanin and the major MIAs, catharanthine and vindoline in silenced leaves. Functional expression of this gene in Saccharomyces cerevisiae confirmed its function as an authentic 7DLS that catalyzes the 3 step oxidation of iridodial-nepetalactol to form 7-deoxyloganetic acid. The identification of CYP76A26 removes a key bottleneck for expression of iridoid and related MIA pathways in various biological backgrounds.

Keywords: 7-Deoxyloganetic acid synthase; Apocynaceae; Catharanthus roseus; Functional characterization; Madagascar Periwinkle; Secologanin biosynthesis; Virus induced gene silencing.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Biocatalysis
  • Biosynthetic Pathways / genetics
  • Catharanthus / enzymology*
  • Catharanthus / genetics
  • Catharanthus / metabolism
  • Cloning, Molecular
  • Cytochrome P-450 Enzyme System / genetics
  • Cytochrome P-450 Enzyme System / metabolism*
  • Gene Silencing
  • Iridoid Glucosides / metabolism*
  • Iridoids / metabolism*
  • Molecular Sequence Data
  • Oxidation-Reduction
  • Phylogeny
  • Plant Proteins / genetics
  • Plant Proteins / metabolism*
  • Real-Time Polymerase Chain Reaction
  • Saccharomyces cerevisiae / genetics
  • Vinca Alkaloids / biosynthesis*

Substances

  • Iridoid Glucosides
  • Iridoids
  • Plant Proteins
  • Vinca Alkaloids
  • secologanin
  • Cytochrome P-450 Enzyme System